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The area was the site of the first building in what is now Hollywood, a three-room adobe house built in 1853 by Don Tomas Urquidez, near what is now the intersection of Outpost Drive and Hillside Avenue. General Harrison Grey Otis, the owner of the Los Angeles Times, acquired the estate from Don Tomás through legal wrangling associated with California's secession to the United States. Near Casa Don Tomás, Otis built a clubhouse on the property for entertaining, which he called "The Outpost."[1]

In 1924, Charles E. Toberman acquired the property. He kept the Outpost name and developed the property as one of several 1920s Hollywood luxury residential neighborhoods. The area became known as an affluent area with many rich and famous residents.[citation needed][2] "Homes had to be designed in Spanish, Mediterranean or California modern style, have red tile roofs, plenty of patios for "outdoor living," and be approved by architectural committee before being built."[3] Most of the original houses have been preserved, and Lower Outpost looks much like it did in the 1920s.

In the 1920s, in the hills above the development, a large sign spelled out "Outpost" in red neon letters 30 feet high. It was intended to compete with the Hollywoodland sign, (which later became the Hollywood sign. At the time, it was the largest neon sign in the United States.[3] The Outpost sign was dismantled during World War II, and the wreckage of the sign was left in place, buried in the weeds. Even the original foundation and electrical junction boxes survived. The twisted remains were identified by hikers in 2002.[1]

In 1967, a homeowners association was formed to combat what residents considered to be inappropriate development. In the 1980s, the group helped to prevent the development of Runyon Canyon.[3]

The Outpost Estates development was one of the first neighborhoods in the country to offer all-underground utilities.[citation needed]

Residents are zoned to three elementary schools, depending upon address: Gardner Street Elementary School, Selma Elementary School, and Valley View Elementary School.[4] All residents are zoned to Bancroft Middle School and Hollywood High School.[5]